Cherry
by watergurl123
Summary: You never forget your first love. Slightly AU. Literati. Rory and Jess meet as children under different circumstances, Jess being slightly older.
1. Chapter 1

**New story, it's AU, and the rest I think you can gather from the text. I hope you enjoy it! Please review, criticism is welcomed.**

Disclaimer: I do not own anything affiliated with Gilmore Girls, except for my original characters.

**Chapter: 1**

**_1992_**

Rory closed her eyes contentedly, a slow smile spreading across her face, exposing most of her teeth. Her tongue reaches up to feel the newest loss, softly probing the soft flesh of her gums.

She'd bounded out of bed like a madwoman, waving her arms triumphantly in the air, a quarter clutched in each fist.

"Mom, she came, she came! The tooth fairy left me two quarters!"

Lorelai let out a small 'oomph' as a mass barreled through the air, landing smack dab in the middle of her stomach. She laughed happily as her daughter's rumpled head popped up over the covers, toothlessly beaming. "She did huh?"

"Yes! Can we go to Doose's and get a gumball? Please?" The eight-year-old gave her best pout, holding her mother's face between her slightly chubby hands.

Lorelai grinned and pulled her daughter close to her, the little girl squealing with delight. "You keeping eating so many gumballs and you won't have any teeth left to give."

Rory blushed and looked at her mom sheepishly. "Please?" She pleaded excitedly.

"Okay. But only one. Your grandmother's been giving me a fit about your 'grotesque junk consumption' as she puts it." Lorelai rolled her eyes. She threw the covers back with a yawn, stretching slowly.

"Thank you Mommy!" Rory smiled and planted a sloppy kiss on Lorelai's cheek. She scurried out of bed and to the doorway. She paused as she waited patiently for Lorelai to crawl out of bed. "Do you think we can get one for Lane too?"

Lorelai let out an incredulous snort of laughter. "Ha, I don't think that's gonna fly kid. Remember what happened last time?"

Rory thought back to when she'd given Lane a gumball without Lorelai or Mrs. Kim's permission, resulting in a very sticky situation involving loss of hair, months of regrowth, and very angry moms. She sighed in resignation. "I guess not."

"Go get dressed." Lorelai kissed the top of her head before giving her a soft pat on the back. "I'll be down in a minute."

Rory chewed happily, pursing her lips to blow a bubble. It popped unexpectedly; cherry flavored gum stuck to her chin and nose. She giggled quietly, stretching her mouth widely to detach the sticky substance. She continued to chew, thinking over her pleasant morning. She swung her feet gently, kicking up pebbles every time the toe of her shoe caught the ground. She locked her arms firmer around the chains, ensuring her balance as she softly turned another page of 'The Indian in the Cupboard'.

Even though she was only in the second grade, her teacher had excitedly informed her mother she was already on a fourth grade reading level. Lorelai had thrown her a party the following weekend, inviting all her closest friends. She'd hung a banner that stated 'My Daughter's a Genius', refusing to take it down for another two whole weeks, until Rory's incessant begging had forced her to concede.

"Be proud kid! This is an amazing thing you did!" Lorelai hugged her close.

"Mom," Rory whined, scrunching her nose and leaning away from Lorelai's clutch, "I didn't do anything. I just 'read on a higher level'." She stated, recalling the words her teacher had used.

"That is something. You are the most amazing girl and I am so proud to call you mine. My little Einstein." She squealed with pride and pulled Rory close, ignoring her shouts of protest.

The sun was warm and refreshing on her porcelain skin. She sighed softly with a private smile. It would be summer vacation soon, which was a little disappointing and exciting all at the same time. She loved school, but she loved playing too.

She fingered a page in her book, ready to turn it, when a sudden strong breeze pulled it from her hands, sending it tumbling across the pebbles.

"Oh no." She frowned and quickly untangled herself from the swings, hopping off to chase after her book.

Just as she crouched to retrieve it, a dark shadow appeared over her. She looked up to see a boy, about the same age as herself, reach down and grab her book off the ground. Thinking he was being polite, she held out her hand appreciatively. "Thank you."

He looked at her outstretched hand before simply walking away with the book in hand.

"That's my book." She called after him shakily.

"So?" He looked back at her

"Can I have it back please?" She stuck her hand out again, rising to her feet.

"No." He answered simply before turning away again.

"But…it's mine!" She spluttered in disbelief.

"You want it? Come and get it." He stood still and stared at her.

She hesitantly approached, shuffling her feet, her knees awkwardly knocking together. She stopped to stand in front of him. She had to look up to see his face; he was half a foot taller than she was. She reached her hand out to grab the book but he easily dodged her attempt, slightly elevating it. She furrowed her brow in irritation before trying again. He began to smile wickedly at each attempt, finally holding the book so high that it was above his head.

Rory began hopping on both feet, stretching her arms as far as they would go. "Give it back!" She shouted. Tears of anger and humiliation began to prick her eyes.

He laughed at her and reached his other hand up, placing it on a random page. He delicately started to pull.

Rory's eyes widened. "Stop it! You're going to rip it!" She pounded a fist against his chest but he remained undeterred.

"That's the point." He pulled quickly and a tear rolled down her cheek as she watched the page flutter to the ground.

"Stop!" She screamed as loud as she could, pounding her fists against any place she could reach. He turned his body away from each attack, his hand continuously ripping out more and more pages.

When one of her blows connected with his nose his demeanor changed from annoyingly wicked to unbelievably angry. He flung the book behind him and pushed hard against her chest.

She flew back and hit the ground, letting out a yelp of pain as her elbows scraped against the dirty rocks. She sniffled as salty tears began to trickle down her cheeks, mixing with her saliva as she cried out in pain and degradation.

"What the hell are you doing Mitch?"

Through her tears Rory could make out another figure standing a few feet away. She sat up a little and wiped her eyes to get a better look. It was another boy; he looked older than the boy who'd stolen her book.

"She hit me!" The boy protested angrily. He reached up and rubbed his sore nose with the palm of his hand.

"Yeah, well she probably had good reason to." The older boy looked around at the scattered pages and ran both hands through his hair. It was then that his gaze traveled over to her. His look was sympathetic as he noticed her bloodied and bruised elbows and tear stained face. "Shit." He mumbled quietly. "What did you do?" His eyes turned accusingly to the younger boy.

"Nothing, I was just playing around!" The younger boy's eyes darted around nervously.

"Playing? Mitch, god, she's bleeding!" He looked angrily at the boy and pointed a hand towards Rory.

"I didn't do it!"

"Man, Mom's gonna kill me when she finds out I wasn't watching you. Why do you have to be such an ass?" The older boy shook his head.

"Mom told you not to call me that." The younger boy sneered at him.

"Well Mom's not here is she?" The older boy said menacingly before taking a step towards the younger one.

"If you hit me I'll tell her!" The younger boy fearfully took a step back.

"You're such a brat sometimes. If you don't say anything, I won't say anything. Deal?" He stopped approaching him and looked at his brother expectantly.

"Fine." The younger said with relief.

"Go home. Dinner should be ready soon anyway." He waved his hand in a general direction and the boy took off.

"Hey." The boy called to Rory. She sniffled and lifted her head to meet his eyes. "Are you okay?"

She nodded wordlessly, though she was anything but. Her elbows were stinging like crazy and all she wanted to do was cry. The boy walked over and offered her a hand. "Here." He said, gesturing to her.

She reached out and took his hand, pulling herself up. "Thank you." She mumbled shyly, her voice hoarse.

"No problem." He looked at her cautiously for a moment.

She avoided his gaze and bent to grab the torn pages of her book.

"I got it." He bent and grabbed a few pages as well before retrieving the book itself. He stacked the pages together and placed them neatly on top of the cover. When he handed them to her he cringed slightly in embarrassment. "I'm sorry about my brother. He's kind of a jerk."

"It's okay." She mumbled with her head down.

"Ah, jeez." He cringed again when he got a closer look at her elbows. The blood was starting to coagulate but some had trickled down onto her forearms. "Are you sure you're okay? That looks pretty bad."

"It's not so bad." She mumbled halfheartedly, glancing at her injuries. "It just stings a little."

"Come on." He nodded his head toward the public bathrooms at the far end of the park.

"I shouldn't…" She trailed off, feeling hesitant to go anywhere with this stranger.

"Don't worry, I just want to clean those before they get infected." He gently took her hand and pulled her toward the bathrooms.

Rory blushed and looked down as the boy's hand wrapped around hers. She trailed behind him, her much shorter legs trying to keep up with his longer ones.

When they stopped by the bathrooms he quickly disappeared into the men's room. A moment later he came out holding a set of wet paper towels and a set of dry ones. He set the dry ones down and gently grasped her bicep. "This is gonna hurt." He said quietly.

When the paper towel made contact with the gashes in her skin she winced and whimpered as he applied more pressure. "It hurts." She whined as a tear trickled down her cheek.

"I know." He stated simply. He looked at her softly before treating her other arm. When he'd cleaned off most of the blood and dirt he gently dabbed them with the dry paper towels. "They didn't have any Band-Aids so you'll need to get some from your house."

"Okay." She nodded miserably. "How come you know how to do this?" She asked quietly. They walked back towards the play area

"Sometimes I have to help my mom out with my brothers." He shrugged slightly as they continued walking.

"You have more?" She asked, glancing at him.

"Two. Mitch and David." He nodded. They made it back to the swing set and sat down simultaneously.

"Why doesn't your dad help?" She asked innocently.

"I don't have a dad." He replied quietly, looking out over the park.

"Oh." She said quietly, faintly registering his sadness. For some reason, it made her sad too. "Me either." Well, technically she _did_, but he wasn't around much.

"Do you live here?" He asked, glancing around, a silent gesture with his eyes.

"Yes, my whole life." She nodded and began to softly kick her feet, swaying back and forth. "Do you?" She looked at him with childishly wide-eyes.

"We just moved here from New York."

Rory vaguely remembered the location of New York. Last week Mrs. Williams had made them go over a map of the United States.

"Do you like it?" She asked politely, staring at her shoes.

"It's…different." He responded cryptically.

"I love it here." She looked out over her town and smiled with pride. Stars Hollow would always be her home.

The boy watched her closely for a moment. His eyes were soft with some emotion she didn't recognize. "What's your name?" He asked quietly.

"Rory Gilmore." She stated confidently. He laughed when she stuck her arm out to shake his hand. She'd seen her mother do it so many times at the inn, she figured it was what everyone did.

"Jess Mariano." He grinned at her.

Rory noticed that his mouth was lopsided. After looking at it for a moment she bluntly stated, "Your mouth is crooked."

He looked away from her and pursed his lips. "It's always been like that."

"How old are you?" She looked at him for a moment.

"Eleven." He glanced at her. He knew she was obviously younger than he was, he just wasn't sure how much. "You?"

"Eight."

He nodded and looked down at the tattered book in her hands. He shook his head at his brother's stupidity. Mitch had a knack for getting into trouble. Jess realized he probably wasn't setting the best example for him back in New York, but maybe things would be different now.

"I can buy you another copy." He waved his hand toward her book.

"Oh, that's okay. I didn't like it very much anyway." She lied unconvincingly.

"I want to." He leaned forward to look at her face.

"Okay." She grinned slightly.

**_1995_**

"You guys, hurry up! Me and Lane are dying out here!" Rory banged on the bedroom door impatiently. She dramatically wagged a hand in front of her face, looking at Lane with a pitiful expression. 'So hot' she mouthed wordlessly. Jess's air conditioning had broken the week before and they still hadn't called a repairman.

"Would you chill? We'll be out in a minute." Jess's aggravated voice responded. "David, I swear to God, if you take that thing off one more time…" Rory heard some scuffling as she listened to what she assumed was Jess attempting to wrangle David back into his bathing suit for the fourth time.

The little boy suddenly burst through the door in all his naked glory, screeching with delight as he rushed down the hallway. David had just turned four last month and was spending his new age as nude as possible.

"Dude, my fucking pants are still down! Shut the door!" Rory and Lane giggled uncontrollably when they heard Mitch's slightly strained and hysterical voice. Without looking, Rory fumbled for the doorknob. Finding it, she immediately slammed the door shut.

"Watch your mouth!" Jess scolded. They heard a yelp as he smacked Mitch on the back of the head.

"Oh, like you ever do?" Mitch rubbed the tender spot and glared daggers at Jess.

"Uh, in front of them?" He said in a 'duh' tone, gesturing with his thumb toward the door, indicating the girls. "Yeah, I do."

"Jeez, you should drop this gentlemanly bullshit. It's obviously an act."

"You say one more thing and I'm knocking you on your ass."

"Oh, so dramatic." Mitch lifted his hands and waved them around mockingly. When Jess glared at him murderously Mitch relented. "Alright, alright, I'm done."

"Shit, I have to go find David." Jess secured his swimming trunks loosely before heading towards the door.

"Don't open the-" Mitch started but was soon silenced by uproarious laughter.

Rory and Lane were doubled over as they looked at Mitch. He was trying to keep his trunks from falling down by knocking his knees together and clutching at them with both hands. They were an old pair of Jess's and were slightly too big.

Mitch's face burned a deep crimson as he scrambled to cover himself. "Close the door!"

The girls quieted down to giggling as they shut the door and walked towards the stairs. "He's such an idiot." Rory rolled her eyes.

"I know. I love him though." Lane sighed dreamily.

Rory made a disgusted noise like she was gagging.

"What? He's so cute." Lane gushed, clasping her hands in front of her excitedly.

"Hardly." Rory replied with the same disgusted tone.

"Hey, just because you have a crush on Jess-"

"I do not have a crush on Jess." Rory whispered harshly, glancing around to see if anyone had heard them.

"-doesn't mean you can deny that Mitch is undeniably, unbelievably, completely, adorably, cute."

"Ugh, he is not cute. He's a complete jerk." Rory grumbled as she crossed her arms.

"You cannot still be holding a grudge about that book, can you? That was three years ago." Lane stretched 'three years' for emphasis.

"Yes, I am still holding a grudge, and I will continue to hold a grudge for the rest of my life." Rory stated petulantly with a huff.

"You're shameless." Lane gave her a look.

"And you're insane." Rory grinned. "So where do you think they're at?"

"Well, I'd have to guess-" Lane started but was cut off by a loud crash.

Both girls smiled widely before stating, "Bathroom."

They opened the door cautiously to find David scampering back in forth in the bathtub, narrowly eluding Jess's grasp.

"Davie!" Jess shouted in aggravation, trying yet again to catch his youngest brother.

"No!" The little boy shouted loudly, ducking out of Jess's arm.

"You have to put this on! I'm not taking you if you're naked!"

"I don't want it!" David yelled, thrusting the suit away from him.

"Fine, then you're staying here! Alone!" Jess stood up suddenly and stalked toward the door. "Come on." He took both girls by their arms and pulled them through the doorway. He slammed the bathroom door closed and leaned against the outer wall, waiting.

Rory and Lane both stood patiently beside him.

About a minute went by before the bathroom door began to hesitantly creep open. Jess molded himself against the wall, holding his breath as the little boy cautiously stepped out to survey his surroundings.

When he was about a foot out Jess suddenly lunged and scooped him up. David went into a frenzy, kicking and screaming as hard and loud as he could.

"Davie, knock it off!" The boy struggled for a few minutes longer as Jess held him the best he could. After a while he finally ceased struggling and limply lay against Jess's shoulder. "Finally." Jess blew out a long breath. He set David on the floor and pulled his trunks on, the little boy being too tired to protest.

"Come on, we gotta get your floaties." He took David by the hand and cautiously led him down the stairs. "Mitch, you ready?" He yelled over his shoulder.

"Give me a sec." Mitch yelled back.

"Jesus Christ." Jess mumbled with a roll of his eyes. He was convinced his brother was the slowest being on the planet.

"No cussing." David shouted up at him, giving him his sternest look.

"Sorry little man." Jess mumbled apologetically. "Rory, can you grab his floaties from the closet?" He turned to look at her questioningly.

"Sure."

Jess released David's hand to grab a pad of paper and a pen.

_'Liz, out swimming, be back for dinner' – Jess_

He turned around to find Lane and Rory struggling to hold David still as they each attempted to apply a floatie to his arms. He chuckled as he watched their irritation grow. "Don't worry, I got it." He grabbed David under his arms and lifted him onto his hip. "He won't let you put them on until we get there anyway." He smirked as they groaned.

"Now you tell us." Rory mumbled as she threw her hands up.

Jess grinned at her for a moment before turning toward the stairs. "Mitch we're heading out!"

"Would you calm down? Jeez, you'd think there was a fire or something." Mitch replied sarcastically as he barreled down the stairs, whipping around the corner as he clutched the banister. "Lets go."

Jess rolled his eyes again as Mitch bombarded his way to the front door. "You're such a prick."

"Don't say that Jessie!" David pointed a finger at him and pouted angrily.

Jess scowled at his little brother's pet name.

"Aw, come on _Jessie_, I thought you were ready to go?" Mitch mocked him, sending Jess his own familiar smirk, an annoying habit Mitch had picked up within the last year.

Jess glared before walking past him, making sure to check him with his shoulder as he passed. Hard.

"Ow! God, you're gonna dislocate it one of these days." Mitch rolled his shoulder uncomfortably.

"That's what I'm hoping." Jess stated with a smirk as he continued to walk to the lake.

**_1997_**

"Mitch, if you're not ready in ten minutes, I'm leaving you here." Jess stood by the door, scowling menacingly.

"What crawled up your ass and died?" Mitch leisurely walked down the stairs with his backpack slung over one shoulder.

"What the fuck did you do to your head?" Jess stared at him with his mouth slightly agape.

"Shaved it."

"You look like a damn skinhead." Jess barely suppressed a laugh.

"What the hell is a skinhead?" Mitch asked in confused irritation.

"Never mind." Jess rolled his eyes. "Just get in the car."

"Why are you in such a rush? We live fifteen minutes from school and it doesn't start for another thirty." Jess shot him a look as they got into their respective sides of the car. "Oh, I get it." Mitch said with a slow grin. "Picking up your girl right?"

"You're calling _Rory_ my girl? She's thirteen for Christ's sake." Jess turned the key in the ignition and backed out of the driveway.

"Stranger things have happened." Mitch shrugged.

"Yeah, like that third eye you're sporting." Jess chuckled as he watched Mitch's face crumble as he opened the passenger side mirror.

"Shit, dude." He grumbled as he stared at the large blemish in the middle of his forehead.

"Should we stop and buy you some concealer?" Jess smirked as his brother shot him a disgruntled look.

"Fuck you."

"You're not my type." Jess flipped on the radio, tuning to a tolerable station.

"So what's up with you guys anyway?" Mitch asked conversationally. He reached into his pocket and pulled out a pack of cigarettes. He tapped them lightly on his thigh before extracting one. He cracked the window slightly and lit it, blowing the smoke out of the side of his mouth.

"Would you cut that shit out? Liz is gonna have my ass if she finds out I let you smoke in here." Jess reached over and plucked the cigarette out of Mitch's hand. He lifted it to his own lips and took a long drag before rolling down his window and tossing it out.

"'Cause you're clearly such a good role model." Mitch rolled his eyes and put the pack back in his pocket.

"Hey smart ass, you wanna ride the bus? Keep talking shit, you'll be there tomorrow morning."

Mitch scoffed but otherwise kept his mouth shut. A moment later he picked up his forgotten train of thought. "You never answered my question."

"About what?" Jess asked apathetically as he turned the car to the right.

"What's up with you two? Something going on?"

"No way. I mean hell; she's still in middle school. Just keeping it friendly."

"Uh huh." Mitch said, unconvinced.

"You honestly think I would try something with someone that young?" Jess gave him an incredulous look, lifting his eyebrows.

"Three years isn't that big a difference." Mitch pointed out.

"It is when one person's still in the eighth grade."

"She's only a year younger than I am."

"Hell, then you date her." Jess said irritably.

"I'm not dating that bitch." Jess looked at him murderously. "Whatever, I'm not dating that _girl_. We hate each other."

"Ah, you're just mad 'cause you couldn't get her all hot and bothered."

"I'm fourteen, I can't get anybody hot and bothered." Mitch mumbled dejectedly.

"You could if you bothered to try." Jess smirked thinking about Mitch's bad luck when it came to girls.

"Aren't you supposed to be discouraging me from this? Preserve my innocence and all that bullshit…" Mitch waved his hand in a vague gesture.

"I could care less about your innocence." Jess turned the wheel to the left and parked the car, finally having reached Rory's driveway. He honked the horn once and settled back in his seat. "Get in the back."

Mitch stared at his brother, flabbergasted. "Oh, come on man!"

Jess just stared at him wordlessly. Mitch sighed and opened the door, slamming it with as much force as he could muster. When he climbed into the back seat he mumbled, "You're a shitty brother."

"Yeah, yeah." Jess replied uninterestedly.

A moment later Rory bounded off her front porch, waving back at her mom who stood in the doorway. She ran up to the passenger window and smiled brightly. "Hey Jess." She said happily before opening the door and settling in. "Mitch." She greeted with less enthusiasm.

"Ror." He said, just to purposefully piss her off. She glared at him for a moment before turning back to Jess.

"I brought you some poptarts." She held up a plastic ziplock bag with two poptarts inside. "The original wrapper broke." She stated sheepishly. "They're apple."

"Thanks." Jess said with a small grin. He took notice of how she blushed slightly before lowering her eyes to her lap.

"Um, Mitch, I brought you some too." She dropped the poptarts over the seat and into his lap.

Jess smirked. She couldn't even be mean to people she hated. When Mitch simply nodded his head Jess cleared his throat slightly and glanced back at him. Mitch rolled his eyes but mumbled, "Oh, uh, thanks."

"Oh my god." She started giggling uncontrollably.

"What?" Mitch asked, looking confused.

"Your head looks like a giant peach." She covered her mouth with the back of her hand to suppress her laughter.

"Shut up." He grumbled, slouching in his seat.

"Is it fuzzy?" She smirked arrogantly.

"Hey, why don't you get your dog a stronger muzzle?" He snapped, looking at Jess, before turning to look out the window.

Rory turned back in her seat and rolled her eyes while Jess shook his head amusedly.

As Jess backed out of the driveway and started down the road, the car filled with an awkward silence. Rory fidgeted with her hands. She continually glanced at Jess as if she wanted to say something but changed her mind at the last minute.

He smirked as he watched her indecisive behavior. "What?"

"Hmm?" She replied, like she'd completely forgotten he was even in the car.

"Something you wanted to say?" He glanced at her sideways, trying to concentrate on the road.

"Well, I just wanted to thank you…you know…for doing this. You didn't have to…" She stared down at her lap, picking at her jeans.

"I don't mind." He replied quietly.

"I mean, I'm not even paying for gas or anything." She rambled uncomfortably.

"I've got it covered." He grinned at her concern.

"You're sure?" She looked at him hesitantly.

"I'm sure." He said with conviction.

"Okay, good." She said quietly, smiling a little.

"So, you nervous?" He asked casually.

"No…well maybe a little." She conceded. "But mostly excited. I mean, it's my last first day of middle school. So that's pretty cool."

"Very cool." He agreed with a slow nod.

"What about you? Excited to be a junior?" She grinned at him.

"Overwhelmingly. This is my year, I can feel it." He said sarcastically with mock enthusiasm.

"I'm serious." Rory said while chuckling.

"It has its perks." He smirked.

"Like?" She drew out the word.

"Well, the whole 'driving' thing isn't too bad."

"I'm a big supporter of it." She giggled quietly.

"You just like having a chauffeur."

"I now have bragging rights." She nodded her head smugly.

"Oh yeah?" He glanced at her with a grin.

"All the sixth graders think you're 'super cute'." She grinned as she used air quotes.

"Hear that Mitch? I'm 'super cute'." Jess smirked at he looked at his brother through the rear view mirror.

"La-de-fricken-da, what else is new?" Mitch grumbled sourly, as he ripped open his poptart wrapper.

"Jealous?" Rory asked tauntingly, turning around to give him a wicked smile.

"Bite me." He snapped.

Jess quickly reached behind him, without looking, and swiftly swung his arm to smack Mitch in the chest.

"Watch it." Jess gave him a stern look through the mirror.

"Asshole." Mitch grumbled as he rubbed his sore chest.

Rory hung her head as she tried to contain her smile. Jess looked at her softly as they both shared a private smile.

As they pulled up to the school Jess parked along the sidewalk, grabbing Rory's bag from the backseat and handing it to her as she stepped out of the car.

"You need a ride home?" Jess ducked his head to see out the passenger window.

"No, Lane and I are going to the library after school." Rory hugged her books close to her chest.

"Gotta get a head start on that book list, huh?" He smirked knowingly.

Rory attempted not to blush as she glanced at her feet. "Not necessarily." She mumbled.

"Right." He grinned at her unease.

"Maybe I was going to pick something up for you, but now you've ruined the surprise." She feigned indifference.

"Rory, I've read everything in that library three times over." He looked at her incredulously.

"Well, that's only because you have the advantage of being three years older than me." She narrowed her eyes at him.

He was about to reply when he spotted a group of girls out of the corner of his eye, giggling quietly with their hands to their mouths. They shyly glanced at him and noticed his gaze, turning away and talking excitedly.

Rory noticed his diverted attention and dropped her eyes, fidgeting slightly. "I should get going." She said quietly.

His eyes snapped back to her face. "I think we have an audience." He tilted his head to the left, gesturing to the group.

"'Super cute' remember?" She shrugged slightly.

Suddenly one of the girls was pushed slightly out of the group, the girls behind her mouthing 'go' repeatedly, ushering her with their hands and giggling excitedly. She shook her head but they just pushed her farther, waving their hands at her in a shooing motion.

She turned to face the car and started hesitantly walking to the driver's side window.

Jess watched her approach and slowly rolled his window down.

When she reached the door she glanced at him and blushed. "Hi Jess."

"Hey." He replied coolly, resting his arm on the door frame.

"I was just wondering, um," she glanced behind her at the group of girls nervously, "if you're not too busy, maybe you'd want to hang out sometime?" She glanced behind her again and swallowed.

Jess mentally rolled his eyes but kept his expression impassive. He glanced at Rory and noticed her looking at the ground dejectedly. "Huh, I don't know. What do you think Rory?"

"What?" Rory's head snapped up to look at him with wide eyes.

"Am I too busy?" The corner of his mouth turned up, almost imperceptibly.

"Oh." She looked from him to the other girl, before looking back at him. "I think he is. You know, with the diner, and school just starting back up. Reading, that can take up time too, I mean, if you read a lot. Which he does. I don't know if you do, but he does, and it can be pretty time consuming." She rambled uncomfortably, wringing her hands. "So…he's busy." She finished lamely, snapping her mouth closed.

"Oh…okay." The girl looked like a mix between frightened and disappointed.

"Sorry." Jess mumbled halfheartedly.

"It's fine. Maybe some other time?" She left the question open ended with a blush, backing away from the window.

"I wouldn't count on it." He mumbled through his teeth but she was already back on the sidewalk.

"Mean!" Rory whispered harshly, sending him a glare.

"What are you talking about? Nice save, by the way." He grinned.

"You put me on the spot!"

"I especially liked the part about reading, very convincing."

"I sounded like an idiot." She huffed.

"I mean, you kinda dropped the ball when you mentioned school, but the reading thing was spot on. Totally sold me." He nodded his head mockingly.

"Bye." She grumbled and turned on her heel.

"Oh, come on. I was just kidding." He chuckled.

"Jerk." She turned back and attempted not to smile.

"And you love it."

"As if."

"I'm sorry, I didn't realize you were from the Valley." He scoffed.

"Ugh, you're right. I feel like my IQ just dropped." She made a disgusted face.

"Ah, wouldn't be such a bad thing." He shrugged.

"Uh, no, I think it would." She said mockingly.

"Someone else could answer a question for once."

"Oh, and I suppose I should just sit in the back and paint my nails?" She narrowed her eyes.

"I hear black is very 'in' right now." He deadpanned.

"You're impossible." She rolled her eyes, backing away from the car.

He smirked. "I'll see you later."

"Later." She waved slightly and turned to walk to the entrance of the school.

His eyes followed her for a moment before he started the engine and peeled out of the parking lot, tires squealing as he rounded the corner.

She looked back over her shoulder and smiled.

"I'm sorry."

Rory whipped around to find the girl who had approached the car standing behind her. "For what?" She asked confusedly.

"My friends made me do it, I didn't realize you and him were…" She trailed off awkwardly.

"Who? Me and Jess?" The girl nodded wordlessly. "Oh, no, no, no. Jess and I aren't…we're not…we're just friends." She stumbled over her words, blushing as she pulled on the straps of her book bag.

"Are you sure? Because it seemed like-"

"I'm positive. There's no way that he would even…" She chuckled nervously.

"But you like him right?" The girl asked shyly.

"What?" Rory's eyes widened.

"Well, he is unbelievably cute, and it seems like he's really nice to you." She grinned sweetly.

"Yes, he is cute, but he's more like a brother. I mean, I've known him for years."

"Oh, okay. I just wanted to say sorry, either way…"

"It's fine." Rory grinned and waved her hand dismissively.

"See ya around." The girl waved before walking back to her friends.

"See ya." Rory's smile disappeared as she walked through the front doors. "Yeah, more like a brother…"

* * *

**Well, this is most definitely the longest chapter I've ever written for anything haha. Since this is an AU, feel free to message me if you have any questions regarding background info. or any confusion over the story. I'd really like to hear feedback on the different relationships I've created. I tried to keep the dialogue appropriate for the circumstances, so please let me know what you think of that. Jess has to behave somewhat differently due to his different living environment, but he still has most of the same traits. More info. regarding his personal life will come in later chapters. Anyway, the more reviews I get, the better I can gauge everyone's reactions, and I'll update even faster. Thank you so much for reading and please review!**


	2. Chapter 2

Finally, a new chapter, and it has some length. Yay. Anyway, I really hope you enjoy it and thank you for reading. Please review!

**Disclaimer: I do not own anything affiliated with Gilmore Girls.**

Chapter: 2

**One month later**

"So, your birthday's coming up." Rory shot another large amount of whip cream into her mouth, her cheeks puffing comically. She swallowed and passed the aerosol can to Jess who sat at his desk chair.

"Uh huh." He mumbled uninterestedly as he tilted his head back and shot some whip cream into his mouth before placing the can onto the desk. He leaned the legs of his chair back slightly, crossing his arms behind his head.

Rory was casually positioned horizontally across Jess's bed, her head dangling halfway off the edge while her feet were planted against the wall on the bed's left side. She pointed her toe and settled it against the calendar that hung beside the mattress, indicating a particular date. "A week from Saturday."

Jess watched her foot gently tap against the paper and rolled his eyes. "I hadn't noticed."

"Really? Because it has a little gold star and says 'Jess's Birthday' on it." She leaned her head back further, grinning widely as she stared at an upside down Jess.

"Who could've done that?" He deadpanned.

"It's just a friendly reminder." She bit her lip playfully.

"How thoughtful." He stood up and walked to the bed, sitting beside her and scooting backwards until he hit the wall. He leaned against it with a content sigh, glancing sideways at her feet which were still planted against the wall beside his head.

"You mock now, but I seem to remember you forgetting quite a few special occasions." She sat up slightly, swinging her body so that her head now rested against his pillows. She stretched her legs out until the tips of her toes rested against his thigh; her knees still slightly bent.

"Name one." He said incredulously as he rolled his head to the side.

"My tenth birthday party."

"I was an hour late." He groaned. "That does not count as forgetting."

"Your fourteenth birthday party."

"That was intentional." He smirked.

"It was cowardly." She narrowed her eyes. "It took my mother three hours to assemble those party favors and Sookie four days to make that cake."

"That _cake_ had a picture of my face on it." He shot her a look. "Which is exactly why I didn't want to go." He closed his eyes. "Besides, you know I don't like surprise parties."

"Well, considering you found out about it and decided to ditch at the last minute, it wasn't much of a surprise, now was it?" She mumbled sourly. "However, what was a surprise was finding you and Katelynn Fernald in a rather compromising position down at Larson's Dock three hours later." She glared at him murderously.

"Ah, I almost forgot about Katie." He grinned nostalgically as he remembered his first experience with second base.

"I wish I had." She grimaced uncomfortably. "I saw things no eleven year old should have to see."

"Sorry about that." He smirked at her unease.

"I mean really Jess, at the dock? Where the swans sleep?" She wrinkled her nose in distaste. "In front of all the woodland creatures and God knows what else probably lurking in the shadows. Have you no shame?"

"Hey, I was a dumb inexperienced kid, heat of the moment, that sort of thing." He shrugged nonchalantly. "Besides, those woodland creatures got a good show."

"I say you're still a dumb kid." She grumbled with a tiny grin.

"Oh, look who's talking Miss Middle School."

"Miss Top Five Percent, thank you very much." She glared and crossed her arms.

He chuckled. "Okay, maybe you're not dumb, but you're still an inexperienced kid."

Her eyes flashed dangerously. "I'm _not_ a kid." She spoke firmly.

"Yes, you are." He glanced at her.

"No, I'm not." She sat up against his headboard, pulling her legs into a pretzel.

"Rory, you're thirteen years old, you're in the eighth grade. You _are a kid_, enjoy it while it lasts." He leaned away from the wall, scooting forward until his feet hit the floor.

"Oh God, I am so tired of your patronizing crap. You're three and a half years older than me Jess, not twenty." She stared at him angrily.

"A lot changes in three and a half years. Do I remotely resemble who I was at thirteen?" He looked at her pointedly. "You've got a lot of growing up to do."

"You are so aggravating. You act like you're so much more mature than me, well you're not." She huffed defiantly.

"Do you have a job? Do you have a car? Do you make your own payments on said car with the money you make from said job?" His eyes blazed. "Do you have to take care of two younger siblings when your mother leaves for weeks at a time to follow around some ridiculous fair?"

"Whatever." Rory looked away, tilting her head so her hair fell over her eyes.

"Or better yet," He started with a sickly sweet tone, "have you ever kissed a guy?"

"What?" Her eyes snapped up to meet his gaze with trepidation.

"Have you ever kissed a guy?" His stare was unwavering.

"That's none of your business." She swallowed thickly.

"I bet you haven't." His tone was challenging.

"I'm not having this conversation with you." She hugged her knees to her chest.

"I thought you were so mature." He widened his eyes mockingly, raising his hands and waving them slightly.

"More mature than you." She said bitingly.

"I think I've disproved that theory." He raised his eyebrows, indicating the conversation they'd just had.

"Sexual experience doesn't qualify as maturity. It can just as easily be stupidity." Jess got a glint in his eye as he moved closer to her. She backed away until she was against the headboard.

"How so?" He asked mockingly, moving until he had her cornered, his hands resting on either side of her feet.

"You know how." She grumbled uncomfortably, blushing slightly at his increasingly close proximity.

"Ah, I think it depends on the people." He leaned forward slightly, reveling in her discomfort, wondering how far he could push this.

"Even mature people can make stupid mistakes." She blushed deeper, her breath becoming shallow.

"Very true." His eyes bored into hers. He was close enough to count each freckle on her face as she stared at him with wide-eyes. His breathing was calm and controlled, a polar opposite to hers. He dipped his head lower and heard her sharp intake of breath. He smirked viciously before suddenly pulling back. "Maybe you're more mature than I thought."

Her face went from shocked expectation to embarrassed anger almost immediately. Her cheeks were a deep crimson as she crawled across the bed, carefully avoiding him. She stood at the end and wrapped her arms around herself. "I'm going home."

"Rory." His eyes softened.

"No, I'm going home." She looked down at her feet and shook her head.

"Wait, stop, stop." He said in exasperation as he reached forward and grabbed her wrist as she moved towards the door. "Stay here." He pulled her back into the room. She tugged her wrist out of his grasp and stared at him with a hurt expression. He stood awkwardly in the center of the room as she looked at him.

"Why…why would you do that?" She fidgeted with her hands.

"I…" He trailed off as he scratched the back of his head.

"I mean, were you just trying to mess with me? Because you think I'm some inexperienced little girl?" She raised her eyes to look at him.

"Well, yeah, I was just messing with you. But come on, we joke around all the time." He stepped forward slightly.

"Not like that."

"I didn't think it was that serious." He looked at her hesitantly.

"Well it is to me." She raised her voice slightly.

A tense pause settled over the room as they stared at one another. Finally Jess licked his lips and cleared his throat. "Okay." He breathed deeply. "I'm sorry. I didn't mean to make you think that I…that we…"

"Yes you did." She said quietly.

He moved back until his legs hit the edge of the bed, sitting down with a tired sigh. He ran a hand down his face before settling it over his mouth as he rested his elbow against his knee. "It was stupid. I shouldn't have done it."

"Why did you?" She sat in his desk chair.

"Just to see your reaction." One corner of his mouth turned up. "You're so innocent Rory." He glanced at her. "Why'd you get so worked up?"

"Because." She looked down at her lap. "Because you were right." She let out a defeated sigh.

"About what?" He asked confusedly.

"I've never kissed a guy before."

"Oh." Guilt racked his body as he looked at her seemingly fragile form.

"Don't act so surprised." She glared at him for a moment. "You already knew."

"I was just being an ass." He winced slightly. "I mean, I didn't actually _know_-"

"You don't have to lie to me, okay?" She mumbled dejectedly. "Everybody knows. Boys don't even notice me."

"That's bullshit." She looked at him, slightly startled. He rarely every cussed in front of her. "Trust me, they notice." He rolled his eyes slightly.

"I don't believe that." She looked away.

"Okay." He was quiet for a moment before he grinned slightly. "Mitch had a crush on you in the seventh grade."

Her jaw hung open slightly. "No."

"Yep." He nodded.

"You're lying." She shook her head in disbelief.

"I swear to God." He held up his hands innocently as he chuckled.

"But…why?" She said completely flabbergasted, her eyes wide.

"Because you're you." He looked at her warmly. She blushed slightly but continued to look at him. "The kid was basically in love with you for an entire year."

"That makes absolutely no sense. We hate each other." She furrowed her brow.

"Rejection's a pretty powerful thing." He smirked.

"How could I reject him if I didn't even know that he liked me?" She sighed.

"Regretting your decision?" He laughed when she looked at him murderously.

"I can't regret something I never did."

"All those 'what ifs'…" He quickly jerked his leg away when she attempted to kick him.

"There are no 'what ifs'." She narrowed her eyes.

"Don't worry, there's still time for a second chance." He held up his hand in mock reassurance.

"That's highly improbable considering there was never a first chance."

"This could be it." He grinned lopsidedly.

"I'm good, thanks." She rolled her eyes.

"I can always set something up if you change your mind." He smirked wickedly.

"I'll remember that." They looked at each other silently. She stood up and walked over to the bed, sitting beside him with a sigh. "Jess?"

"Hmm?" He glanced at her.

"Do boys really notice me?" She asked quietly.

"Definitely."

"How do you know?"

"I noticed you, didn't I?"

"That's different." She rolled her eyes. "Your brother beat me up on the playground, that's not exactly a romance for the ages." She grinned when he chuckled beside her. "So how do you really know?"

"Because I see it. All the time." He shrugged. "You're far from ugly, Rory, if that's what you're wondering." He smirked as she bit her lip. "And you've got a killer personality on top of it. So don't worry, guys are there." She looked hesitant so he gently nudged her with his shoulder. "Trust me."

"I guess." She leaned against his shoulder with a sigh. It was quiet for a moment as a comfortable silence filled the room. A moment later, Rory leaned away from Jess, looking up at his face. "Have you been with a lot of girls?" She winced slightly at the phrase.

"What do you mean?" He furrowed his brow slightly as he cleared his throat uncomfortably.

"Well, I would ask if you've kissed a lot of girls, but if Katelynn Fernald is any indication, you've done more just…kissing." She finished lamely with a disgruntled expression.

"Why?" He leaned away from her.

"I don't want…details or anything," she started cautiously, "I just want to know…what it's like."

"I don't think I'm the person you should be asking." He ran a hand through his hair.

"Why not?" She asked innocently. "I mean, you have experience right?"

"Yeah, but," he stood up, laughing uncomfortably, "I think my perspective would be a little different than what you're looking for."

"I'm not looking for any certain perspective." She shook her head.

"Trust me, you are." He looked away. "I'm a guy Rory, my thoughts on the subject aren't exactly 'pure'."

"I told you I don't want details."

"Wouldn't you be more comfortable talking to Lorelai about this?"

"Would you be comfortable talking to your mother?" She gave him a disgusted look.

"No, probably not." He said with a resigned sigh. "What do you want to know?"

She contemplated for a moment. "When was your first kiss?"

"Right before we moved to Stars Hollow." He sat back on the bed.

"You were eleven?" Her jaw dropped.

"Don't judge." He grinned slightly. "It's not like it was some mind blowing experience, just a little peck. But I guess you could call that my first kiss."

"Who with?" She scooted until she was resting against the headboard.

"Samantha…something." He waved a hand dismissively.

"How romantic." She mumbled.

"At least I got the first name." He scratched the back of his head.

"What was it like?"

"Nothing special, just a kiss." He shrugged.

"You are so not helpful." She huffed irritably.

"I told you I wasn't the right person for this." He leaned against the wall, lifting her legs and placing them across his lap.

"Come on, I know you have emotions. I've _seen_ them, first hand." He chuckled. "You had to have felt something, anything."

Jess was quiet for a moment. Finally he nodded his head thoughtfully, "I was nervous. Terrified, actually." His lips twitched.

"Wow, that's surprising." He glared at her. "No, I'm being completely serious, that's really surprising. You're so…confident."

"Now I am." He laid his forearms across her shins. "But I've had practice."

"Lovely." She grimaced slightly. As he opened his mouth to respond she interrupted him. "I know, I know, 'you're not the right person for this', blah, blah." She waved her hands mockingly.

"What a flattering impersonation." He said sarcastically.

"You need to be knocked down a few pegs anyway." She smiled gently.

"See, I knew there was a reason you were my best friend." He rolled his eyes. "Are we done?" He gripped her legs to lift them but she wiggled out of his grasp.

"No." She said firmly. "Is this making you _that_ uncomfortable?"

"Why are you so calm?" He countered.

"Because I'm not the one being questioned." She smirked.

"Sadist." He mumbled.

"Was it your typical first kiss?"

"Depends on what your definition of typical is." He settled back against the wall.

"You know, like, the movie style first kiss. You stare at each other, lean in really slow, kiss and then some sappy instrumental song plays in the background?"

"Not at all." He chuckled. "It, uh, couldn't be farther from that. Basically, we, uh, both looked at each other, said 'You've never kissed anybody?' 'Great, me neither' leaned in, bumped noses, peck, it was over." He explained very quickly with as little detail possible.

"That is the lamest first kiss I have ever heard of." Rory giggled.

"Told you it was nothing special." He grinned.

After quieting down, she breathed a deep sigh of contentment. "So…it was good?"

"It was good." He nodded with a smile, amazed at her ability to pick up on his almost imperceptible emotions.

"Sounds like it was." She bit her lip.

"The lame stuff usually is." He stated wisely.

"Cheeseball." She laughed when he glared at her.

"Hey, if you want me to be a dick about it…" He held up his hands.

"No, I like you being cheesy. It's cute." She smiled softly. "Doesn't happen very often."

"I'll keep that in mind." He rested his palms on her legs, giving them a sight squeeze. "So, we done?"

She sighed. "I guess."

"Thank God." He mumbled. She swung her legs off of him and sat up so they were hip to hip. Jess was leaning forward with his elbows rested against his knees, looking back over his shoulder slightly to see her face. They looked at each other for a moment and smiled before he turned his face forward.

Rory looked at his back, watching as the thin fabric of his T-shirt conformed to every contour of his body. Her eyes traveled to the back of his head, staring at the hair at the base of his neck. Finally her gaze traveled down to his hands which were clasped in his lap. She breathed deeply as she made a decision. Uncrossing her arms, she slid one hand down to meet his, gently prying them apart. She gently threaded her left hand with his right, his much larger fingers enveloping her slender ones.

Jess looked down at their joined hands before turning to glance at Rory. His look was questioning as he stared at her openly.

"Jess, I," she cut herself off as she swallowed thickly, "I want you to be my first kiss."

His eyes widened slightly as he stared at her. "Now, or-" He started hesitantly.

"No, not now. Maybe not for a while, but…eventually." She lowered her eyes, blushing profusely.

"Rory, you can't…you can't know something like that." He shook his head. "I mean, what if a year from now you meet some guy, then you'll want him to be it. You shouldn't have anything holding you back."

"I won't…change my mind." She shook her head slightly. "I want you to be it."

"You're sure?"

"I'm sure." She squeezed his hand lightly.

"Okay." He nodded. "You should probably go." He said quietly.

"Yeah, it's kind of late." She released his hand and stood up from the bed. "I'll see you tomorrow night?"

"Tomorrow…" He trailed off, trying to think if he had any preexisting plans. "I think I'm free." He blew out a slow breath.

"Movie night, seven o'clock, junk consumption is mandatory." She pointed at him and grinned as she backed towards the door.

"At least let me pick the junk this time." He groaned.

"Fine, you pick, but it better be something other than fifty pounds of Smarties." She looked at him pointedly.

"I can't help it, they're addictive." He smirked. "Later."

"Bye Jess." She smiled before exiting the room.

He fell back onto the bed, his arms lying limply at his sides. Rolling over he buried his face in a pillow, letting out a frustrated groan. Turning onto his back, he stared up at the ceiling, running a hand through his hair. "Fuck."

A knock sounded on his door and he grumbled irritably. "Yeah?" He called out.

"Hey sweetie." Liz stood in the doorway, grinning from ear to ear. "Did Rory just leave?"

"Yep." He sat up from the bed, rubbing his neck.

"Aw, that girl is something else. Cutest thing I ever saw." Liz walked further into the room. "How she puts up with you is beyond me." She smiled teasingly.

"Did you need something Liz? I'm about to head out." He cleared his throat. Standing from the bed he coughed lightly. He rubbed his chest for a moment as he walked to his dresser. _I really need to cut back_. He grabbed a pack of cigarettes from the top drawer and stuffed them in his back pocket.

"Can't I just talk to my son?" She walked up and grabbed him by the shoulders. He avoided her gaze but stopped moving. "Come on, let's sit." She walked over to the bed and forced him to sit beside her. "So," she began enthusiastically, "how's life?"

"Same old, same old." He mumbled halfheartedly.

"School's good? Not flunking out are ya?" She stated bluntly as she patted him on the back.

"Got it covered." He stated evasively.

"That's great. You're such a smart kid, you're gonna do good in life." She ruffled his hair slightly. He scowled and leaned away. "Got yourself a girl yet?"

"No." He stated curtly.

"What about Rory? She seems interested." She smiled knowingly.

"She's thirteen." He stared at the wall uninterestedly.

"Ah, that's nothing." She waved a hand dismissively. "She could be good for you."

"I've gotta go." He stated hastily but she grabbed his arm, preventing him from standing.

"Hey, just, hold on a second." He sighed but relaxed back onto the bed. "There is something I wanted to ask."

"What?"

"Well, the fair is starting back up in few weeks and I was thinking," she paused dramatically, "maybe I could try and sell some of my new jewelry this year, make some extra cash. I tell ya, the women around here _love_ my new designs." She held up her hands excitedly. "So I figured the Renaissance circuit would probably love 'em too, but, the thing is, I only have enough supplies left for thirty pairs…"

He sighed. "How much do you need?"

"About eighty. I need some new wire and beads, those can get pretty expensive." Jess stood and walked to his dresser. Locating his wallet, he pulled out four twenties and handed them to Liz.

"Aw, thank you baby. I don't get paid for another week and the guy I get my supplies from gives me a great deal if I buy in bulk, but he said he wouldn't get another shipment in until next month." She rolled the bills and put them into her pocket.

"I'll pay you back next week, I promise." She stood and walked to him, holding his face in her hands. "I don't deserve a son as good as you." She kissed him on the forehead and smiled before letting him go.

His jaw tensed and he nodded silently. "When are you leaving?" He stared at a stain on the carpet.

"The fair leaves in four weeks."

He closed his eyes tightly and ground his teeth. "Please tell me you're gonna be here for David's play."

"Shit, is it that soon?" She put a hand to her forehead.

"Damn it, Liz, you _have_ to be there." He turned around and gripped the edge of his dresser tightly.

"Okay, don't worry, I'll work something out. I will definitely be there." He turned back and stared at her coldly. "Cross my heart." She placed her palm over her chest.

"Don't make this promise if you can't keep it." His body was rigid as stone as he looked at her intently.

"I wouldn't miss it."

Jess nodded doubtfully but didn't make any further comments. He grabbed his wallet and keys, shoving them in his back pocket as he walked towards the door. "I'll be back later."

"Not too late, you have school in the morning." Liz called to his retreating form. "Jess, you hear me?"

"I heard you." He crept through the hallway, careful to be as quiet as possible when he passed David's room, afraid of waking the fitful sleeper. He glanced at the clock in the living room, noting that it was already past nine. He stopped for a moment and looked at the mantel above the fireplace, his eyes fixed on one particular item. It was the only portrait of the entire family, taken right after they'd moved to Stars Hollow. David was still a pink bundle nestled in Liz's arms as she grinned enthusiastically at the camera. Mitch was half-in, half-out of the picture, as he'd decided to jump in at the last minute; his right arm outstretched in an attempt to obscure the camera's view. Jess was in the background, seated on their leather loveseat, a book resting in his lap as he looked at the camera with a bored expression.

"You leaving?" Jess looked to his left and saw Mitch peeking out of the kitchen doorway.

"Yeah." He pushed open the screen door. "I'll be back."

"Can I come?"

Jess closed his eyes for a brief second and sighed. "Not tonight Mitch."

Mitch looked slightly hurt for a moment before shrugging. "Whatever."

Jess opened his mouth as if to speak but quickly shook his head and turned towards the door. Walking outside, he extracted a cigarette from the pack in his pocket and lit it before he'd even reached the car door.

He drove aimlessly for a half-hour, smoking and listening to the radio. Driving down the street, he made a quick decision and parked haphazardly next to the bus stop. Digging in the cup holder, he pulled out three quarters and walked to the payphone.

Depositing the money, he quickly dialed and waited impatiently as it rang, stuffing his free hand in his pocket.

"Hello?" A tired female voice answered on the fourth ring.

"Hey Nicole."

"Who's this?" She grumbled.

"It's Jess." He said quietly, glancing over his shoulder.

"Oh…" He could hear the recognition in her voice. "Hey. What's up?"

"Nothing much." He replied vaguely.

"You okay? It's kind of late." He could hear some muffled shuffling as she slid off her bed.

"I'm fine." He mumbled. He paused a moment before asking the main question on his mind. "Are your parents home?"

There was a long silence. "They're in Boston." She replied with a knowing edge to her voice.

"I'll be over in ten minutes." He ran a hand through his hair.

"Okay." She replied before they both hung up.

He rolled onto his back, taking several deep breaths, waiting for his heart to steady. Nicole slid from beneath him, pushing a hand through her hair, removing stray pieces that were stuck to her damp forehead.

She leaned up on an elbow, her eyelids heavy with exhaustion and pupils dilated with a post-coital calm, and looked at him tiredly. He kept his eyes toward the ceiling, running a hand over his face before placing it behind his head.

She reached up and gently tugged on his hair before letting her hand run down the side of his face, tracing the line of his jaw.

He glanced at her hand before looking at her with a nearly blank expression, the only discernible emotion being the last remnants of his fading lust.

"Hi." She said quietly.

"Hi." He mumbled, turning his head an imperceptible amount.

He looked at her a moment before turning his eyes back to the ceiling. He took a deep breath, trying to calm the unrest and unexplainable twinge of emotion that was tightening his throat.

She wrapped an arm around his waist, still moist with sweat, and traced small patterns on his side. "What's wrong?" She asked quietly.

"Nothing." His voice was empty.

"You seem upset." She grasped at straws.

"I'm fine." His answer was curt with irritation.

"Okay." She whispered dejectedly, her hand ceasing its movements.

A feeling of guilt racked his body but he tried his hardest to ignore it. He swallowed thickly and clenched his jaw, nibbling on the inside of his lip. She couldn't help him, he decided. _She can't fix this._

"I should go." He mumbled, the inevitable truth of the situation being too much to stomach.

"You could stay." Her voice held a note of hope.

"I have to be somewhere." He stood from the bed, pulling on his clothes.

"It's midnight." She glanced at the clock incredulously.

He chose not to reply as he sat on the edge of the bed, pulling on his boots. She scooted forward, wrapping an arm around his waist and pressing her bare chest into his back. He tensed noticeably, ceasing his movements. "Nicole…" He whispered.

She swallowed and dropped her arm.

He was still a moment longer before he finished his task, rising to look at her. The sheet was gathered around her hips, leaving her torso completely exposed as she leaned on her arms, looking up at him bleakly.

He licked his lips and quickly leaned down to kiss her forehead before backing towards the door. "I'll see you some other time." The words felt sour on his tongue

She nodded, her eyes downcast, pulling the sheet over her stomach.

He stopped at the doorway, looking back at her. "I'm…" He didn't know what to say.

Saving them both from further discomfort, she let him take the easy out. "I'll see you." Her voice was empty, but she offered a sad grin, before turning over and pulling the blankets over her shoulders.

He blinked before walking out the door.

Sitting in the car, he gripped the steering wheel tightly, looking out the windshield unseeingly. A moment later he started the engine and drove to the only place he could think to go.

He parked down the street, not wanting to wake her mother. Walking onto the porch, he winced slightly when the old wooden planks creaked. He tiptoed to her window, leaning down to glance inside. Her curtains were drawn but there was a crack big enough that he could see her peacefully sleeping inside. He debated leaving at that very moment, wary as to whether he should wake her at this hour, but something had his feet firmly planted to the ground. He took a deep breath before knocking lightly.

She stirred and glanced around, her eyes confused. He knocked a second time and she looked toward the window fearfully. After her eyes adjusted to the darkness, she could see his form through the glass and breathed a sigh of relief. Crawling out of bed slowly, she stumbled over to the window, yawning widely. Pushing aside the curtain, she opened the window slowly, leaning on her thighs. "Do you know what time it is?" Her voice was raspy with sleep.

"Late." The corner of his mouth twitched.

"What are you doing here?" She rubbed her eyes with the heels of her hands.

"Can I come in?" He nodded toward the room, ignoring her question.

"Tell me what you want first." She crossed her arms.

"To come in." He looked at her beneath long lashes.

"Ooh, nice try." She blocked the window with her body. "Would you like to buy a vowel?"

"Rory," he sighed in exasperation, "seriously, I just…wanna come in." His eyes searched her face.

She breathed a long sigh before stepping back, allowing him enough room to slip through. "You're not staying long." She walked to her bed, lying back on it.

"Wouldn't dream of it." He mumbled as he sat by her feet. He rolled his tense shoulders, before running his hands over his face, before finally resting his chin on his closed fists.

"What's wrong?" She observed him silently, noticing his sketchy behavior.

"Nothing." He replied, though he knew that wouldn't be enough.

"You're lying." She said simply, sitting up to wrap her arms around her knees. "Something is. You wouldn't be here if it weren't."

"It's nothing important." He conceded slightly.

"I don't believe that." She pulled her legs beneath her so they were now sitting hip to hip. "Tell me." She demanded.

He remained silent so she sighed in annoyance. "Fine, you want me to guess? I'll guess. School?" She started lamely.

He snorted and shot her a look as if to say 'seriously?'

"Hey, I'm trying to eliminate all possibilities." She defended. "So, not school. Work?"

He shook his head.

"Hmm, girlfriend?" She glanced at him.

He looked at her irritably. "You know I don't have one."

"Well, maybe that's the problem." She grinned slightly.

"Hardly." He scoffed, thinking of where he'd just come from.

"Okay, jeez, you don't have to be a pig about it." She scrunched her nose. She was silent for a moment as she debated other possibilities. As a thought crossed her mind she grew incredibly still and quiet, her entire demeanor changing. She licked her lips. "Your mom?" She asked quietly, her expression somber.

He silence was the only confirmations she needed. "What happened?"

"She's leaving again." He replied quietly.

"For how long?"

"Don't know." He shrugged.

She looked at him gently before placing an arm around his back and leaning her head on his shoulder. "I'm sorry."

"Yeah, me too." His tone was bitter.

"Well, if you need any help, you know, while she's gone…my mom and I can always…" she trailed off, unsure of what to offer him.

"I can handle it." He shook his head.

"Do Mitch and David know?" She looked at him carefully.

"I don't think so." He closed his eyes.

"Maybe it'll only be a week this time." She said with false hope.

"Doubtful." He clasped her free hand.

"You're a good brother to them." She stated truthfully. "They look up to you."

He nodded but made no comment.

She squeezed him tighter. "I'm really sorry."

"Don't be." He leaned away from her, standing. "I'll deal with it, whatever." He tried to say with nonchalance but she could see how it was tearing him apart.

"Okay." She said quietly as she stood. She chewed on her lip and looked at him timidly.

"I'm gonna go." He gestured toward the window with his thumb. "Sorry I woke you up."

"It's fine." She dismissed the thought with a shake of her head. "I'll see you tomorrow." She said as he crawled through the window.

"Yeah. Goodnight Rory." He leaned down and smiled at her halfheartedly.

"Goodnight Jess." She softly smiled back before shutting her window.

* * *

**Okay, so I tried to sneak some background information in there, but not make it so blatantly obvious haha, if that's even possible. Anyway, I hope you enjoyed it. Please review and tell me whatever you think! I encourage criticism. Thanks for reading.**


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